Vacation rentals with outdoor seating in Chilmark

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Popular amenities for Chilmark outdoor seating rentals

House rentals with outdoor seating

Top guest favorite
A bright and airy dining area features large windows that invite natural light, showcasing scenic views. A round wooden table is surrounded by four chairs, while the ceiling displays striking vaulted beams. A cozy blue seating area is nearby, enhancing the openness of the space.
Home in Woods Hole
5 out of 5 average rating, 63 reviews

Modern Marvel in Woods Hole - Walk to town & ferry

DoreenRating, 5 stars1 week ago
We traveled with 4 couples who have know each other since HS, 40 years ago. It was a great home to relax and catch up. The house is lovely and we loved that we each had our full bath! I highly recommend this home and this location.
Top guest favorite
A three-story house is nestled within a lush green yard, showcasing two expansive outdoor decks adorned with comfortable seating. Sunlight filters through trees, creating a serene atmosphere. The lower level features walk-out access, enhancing the connection to the outdoor space surrounded by natural landscaping.
Home in Tisbury
4.98 out of 5 average rating, 272 reviews

Sunny, Spacious Vineyard Retreat

LindaRating, 5 stars5 days ago
Fran's house is lovely, everything one needs for a fabulous stay. She is a very good host - responsive and informative. She lives on the prpoerty but we never saw her. We had a really great stay!!!
Guest favorite
A spacious living area showcases wooden flooring and high ceilings with exposed beams. Large windows fill the space with natural light, while a cozy sofa and a white coffee table invite relaxation. A kitchen area is visible in the background, providing a functional and open layout.
Home in Tisbury
4.94 out of 5 average rating, 133 reviews

Vineyard Haven Walk to Ferry

WendyRating, 5 stars1 month ago
We totally enjoyed our stay! Our first night we stayed out due to rain but that didn’t stop a grand time cooking at home! We had everything we needed to cook in and relax! The accommodations were perfect for the 3 of us with each of our own rooms. We enjoyed the turkeys and all their antics-lol. Thank you for a great place to stay! We will be back!
Top guest favorite
A bright living space features two orange chairs and a large blue ottoman. A wall-mounted smart TV is visible, and a dining area with colorful chairs and a chandelier is located nearby. A ladder leads to a loft area above the seating.
Home in Falmouth
5 out of 5 average rating, 62 reviews

Waterfront-Kayaks & SUPs-Firepit-Pet OK-Kingbed

JudithRating, 5 stars1 month ago
Beautifully remodeled home, lovely setting on a large pond. Everything was clean, the kitchen was well stocked. I am an avid cook/home chef and appreciate the decent cookware. So many places have understocked kitchens and wounded cookware. Comfortable King bed. Thoughtfully decorated. Nice quiet neighborhood. We travel with our 13 year old boxer who has traveled the country and we appreciated the one level living. We did not mind being farther from town, we love the wildlife and the beautiful swan swimming on the pond! The host, Benjamin, was easy to get ahold of, though we had no issues with anything at all. The booklet on Salt Crystal that was sent ahead to us was extremely helpful to us! We would definitely stay here again!
Top guest favorite
A charming home is framed by a gravel pathway leading through landscaped gardens. The exterior features a warm wood finish, complemented by thoughtful plantings and natural stone accents. A wooden trellis adds vertical interest beside the entrance, enhancing the welcoming atmosphere of the property.
Home in Edgartown
5 out of 5 average rating, 14 reviews

Quaint Roomy Ranch

MeaganRating, 5 stars4 months ago
House was very cozy. Nice quiet neighborhood. Beds were very comfortable. I would not hesitate to stay there again.
Guest favorite
A modern kitchen is showcased, featuring stainless steel appliances and a large island with seating. Natural light fills the space through a patterned curtain, complementing the blue and white decor. A cozy seating area includes a light-colored sofa and a coffee table, enhancing the room's functionality.
Home in Edgartown
4.92 out of 5 average rating, 151 reviews

✅Beach ✅Downtown ✅Restaurants/Bars ✅Bike Path

DanielRating, 5 stars2 weeks ago
Great location just over 2 miles (3.5 K) from the heart of Edgartown. There is a little bit of road noise per the other reviewers but it minimal, especially at night. The place is very clean and has everything you need for a comfortable stay. We were 4 adults, stayed for 2 nights, and had a vehicle so were able to easily explore the island from this location. Other than breakfast, we ate out (lots of great places to eat on MV) but the kitchen is fully equipped should you choose to eat in. The nearby Stop and Shop grocery store is well stocked.
Top guest favorite
A spacious wrap-around porch is shown with comfortable seating, offering panoramic views of the waterfront. The warm glow of sunrise reflects on the water, and a distant bridge is visible under a clear sky. The setting invites relaxation and enjoyment of the serene environment.
Home in Somerset
5 out of 5 average rating, 131 reviews

Beachfront W/ HotTub,Sauna, Pool & Panoramic view

DanielaRating, 5 stars2 weeks ago
This house was exactly how it was described. As soon as you pull into the drive way you see a gorgeous house. Checking in was a breeze. Gary gave us the pin and we were all set to access the house. The pictures do not do this house justice. Everything was spotless. We felt like we were home. Our host Gary was so sweet and responsive. He created this welcome booklet which helped so much. We couldn’t have asked for a better weekend away. We cannot wait to come back and stay at Gary’s house. Thanks Gary for everything!
Guest favorite
A welcoming entrance is framed by a neat sidewalk leading to a white front door, flanked by two windows. The exterior showcases classic shingle siding, with vibrant flowering shrubs and a well-maintained lawn adding charm to the inviting facade.
Home in Edgartown
4.98 out of 5 average rating, 178 reviews

20-minute walk to Edgartown Village!

RyanRating, 5 stars3 days ago
We had a wonderful stay at Madison’s place! The home was fantastic for our family of four. Tastefully decorated, very comfortably laid out, and the kitchen is fully stocked. Madison left a welcome gift that was much appreciated, and proactively communicated throughout our stay. There are a few restaurants and shops within a 5-min walk, and downtown Edgartown is about a mile away. Would 100% stay here again if we come back to MV!

Apartment rentals with outdoor seating

Superhost
A charming waterfront building with a distinct blue facade features multiple balconies lined with railing. A lively outdoor dining area is visible on the lower level. Surrounding structures reflect a lively coastal atmosphere, with clear skies and people enjoying the vibrant setting.
Apartment in Oak Bluffs
4.88 out of 5 average rating, 153 reviews

WATERFRONT PENTHOUSE OAK BLUFFS

JustynRating, 5 stars9 months ago
We spent our anniversary at Leslie’s place and it was a beautiful! The views and location was like no other and we would book again! Leslie was very responsive and even left us some dinner when we came in late from the ferry. The restaurant staff were friendly and it was everything described in the listing. We didn’t want to leave!
Top guest favorite
A spacious garden area is shown, featuring a large tree providing shade alongside the main residence. Lush green grass extends throughout the yard, complemented by colorful flower beds. A stone border outlines the garden, enhancing the serene outdoor environment.
Apartment in Westport
4.94 out of 5 average rating, 271 reviews

15 Acres of Open Fields & 15 Minutes to the Beach

TiffanyRating, 5 stars1 week ago
We went to stay at Cathleen's for my very first big ticket concert. We were met by her mom Judy who was very kind and helpful. The place was very homely , very clean, had a beautiful garden and the property is stunning! We had a great stay, would go back! And highly recommend!
Top guest favorite
A cozy sleeping area features a light-colored headboard and a decorative throw pillow resting on a neatly made bed. Natural light is filtered through sheer curtains and vibrant floral drapes, enhancing the serene ambiance of the room.
Apartment in Fall River
4.98 out of 5 average rating, 196 reviews

Taylor's Pharmacy Guesthouse

Emily MurphyRating, 5 stars1 month ago
We had a perfect stay — travelling with a toddler can sometimes be challenging but Debora provided everything we needed to make the stay comfortable (cot, high chair, bath, even cutlery!) and it really felt like a home away from home. The airbnb was spotless, it’s a good location in Fall River walking distance from a playground, parking was super easy, and we loved our stay.
Top guest favorite
A kitchen area features a bar with three wooden stools, inviting casual dining. Hanging pots and pans are showcased above the counter, while a vase of red roses adds a touch of color. A brick wall complements the white cabinetry and appliances.
Apartment in Tisbury
4.93 out of 5 average rating, 125 reviews

Harbor view apartment, a quick walk from the ferry

KatherineRating, 5 stars2 weeks ago
Mark's place was exactly how it appeared in photos. Great, walkable location. Easy to get to restaurants on Main St. There's a place to rent bikes just across the street. The stay was comfortable, quiet, and exceeded expectations. Thank you again, Mark!
Superhost
A cozy living area is presented with a dark couch and a wooden dining table accompanied by black chairs. A TV is situated on a light-colored media unit, while bookshelves filled with books line one wall. Natural light filters in through sheer curtains.
Apartment in Fairhaven
4.77 out of 5 average rating, 109 reviews

Main Street on the Park

VivekRating, 5 stars3 weeks ago
Beautiful and well-maintained place. We had a minor issue, but Jonas was very proactive in resolving it. Felt right at home.
Guest favorite
A small outdoor balcony features a sleek table set for two, adorned with vibrant blue cushions on barstools. In the background, the view reveals a shimmering bay dotted with boats and framed by trees, showcasing the serene waterfront environment.
Apartment in Wareham
4.94 out of 5 average rating, 159 reviews

⭐ Gorgeous Beach Views -- The Sand Dollar Suite

GinaRating, 5 stars1 month ago
Relaxing girls get away weekend. Amazing views, very walkable and friendly town and beach. (Delicious local ice cream shop- vegan options too!). The perfect place to relax, catch up with friends, and make some delightful memories.
Top guest favorite
Aerial view showcases a peaceful coastal neighborhood, with homes set against a backdrop of the ocean. The green lawns and sandy shore create a harmonious landscape. Soft clouds drift above, and the water glistens under natural light, enhancing the serene coastal environment.
Apartment in Little Compton
4.96 out of 5 average rating, 320 reviews

Home by the Sea

LaurelRating, 5 stars1 month ago
This was our second stay and there's a reason we came back! The space is cozy and comfortable - We especially appreciated the easy flexible check in and snacky snacks and coffee. Thank you Norm!
Guest favorite
A coastal-themed painting is displayed near a bright blue door. The artwork features sandy shores and gentle waves, complemented by tall grasses, conveying a serene beach scene.
Apartment in Falmouth
4.95 out of 5 average rating, 171 reviews

Your Private Garden

VeronicaRating, 5 stars2 weeks ago
We had a lovely time at Mary Alice’s place. She was incredibly kind, helpful, and responsive before, during and after our stay. Even though we weren’t able to meet in person, she made sure we felt welcomed and had what we needed. She also offered flexible checkin/checkout which we didn’t end up needing, but it was nice to have as an option! The location is a quiet and cozy neighborhood that offered us privacy but was also walkable to the main street. Many thoughtful touches incorporated into the place - I can tell that she treats her home with so much love and care, and it shows! Would recommend!

Condo rentals with outdoor seating

Guest favorite
A two-story house is depicted, featuring a light-colored exterior with multiple porches and large windows. A spacious yard is visible, framed by greenery. The porches, supported by columns, provide outdoor seating, inviting relaxation. Power lines stretch across the clear blue sky above the structure.
Condo in Tisbury
4.98 out of 5 average rating, 50 reviews

Short Walk into Town - Nice Comfortable Reasonable

AshleyRating, 5 stars10 months ago
Walkable to all local shops. Unit was clean and the kitchen was fully stocked with all items needed to prepare and enjoy a meal.
Guest favorite
A spacious pool area is enclosed by a white fence, surrounded by lush greenery. Lounge chairs are positioned around the edge of the inviting water, with trees and houses framing the scene in the background. The sky transitions to soft hues during sunset.
Condo in Vineyard Haven
5 out of 5 average rating, 21 reviews

Relax....You're on Island Time......

JocelynRating, 5 stars10 months ago
Lovely home and well outfitted for our stay. Conveniently located on well maintained grounds.
Superhost
An open lounge area features a comfortable seating arrangement, including a white sofa and patterned armchair. A wooden coffee table sits at the center, complemented by a glass side table. The room is illuminated by track lighting, with windows providing natural light and views.
Condo in New Bedford
4.68 out of 5 average rating, 37 reviews

Crow's Nest Down Town New Bedford.

KateRating, 5 stars9 months ago
Phil's place is ideally located in New Bedford for beautiful walks along the pier and throughout the downtown historic district. Close to great restaurants and coffee shops. The crows nest offers the best views of the downtown! Phil was very helpful and responsive. Easy to get checked in and out.
Superhost
A wooden sign is displayed on a light-colored wall, featuring the phrase 'Heaven is a little closer by the Beach' in white lettering on a teal background. The sign is framed in a rustic white border, enhancing its coastal charm.
Condo in West Dennis
4.84 out of 5 average rating, 51 reviews

Hidden Hideaway

JennyRating, 5 stars7 months ago
The location is fabulous and very close to many amenities - coffee, groceries, restaurants and the beach. While it was a small space, it was well laid out, comfortable to be in, very clean and had a respectable kitchen for its small size (which I used). Devon was very proactive and friendly when I asked him about the microwave not working - I had missed that it wasn't plugged in! The condo was very quiet at night even though it is close to a road. I will definitely return to Devon's place should I need to travel there and it is available.
Guest favorite
A two-story house is set on a lush green lawn, framed by vibrant flowering bushes. Stone steps lead up to a white front door, flanked by large windows. A partial second-floor deck is visible above the entrance, with a clear blue sky overhead.
Condo in Tisbury
4.9 out of 5 average rating, 73 reviews

Sunny 2bedroom condo w pool, walk to town

ShayRating, 5 stars7 months ago
We had a great time at Leah’s place. She is a terrific communicator, immediate responses. She also reached out to share about local fun events that were happening during our stay. So nice! We would definitely stay there again.
Top guest favorite
A private deck features a glass-topped table set for dining, surrounded by black metal chairs. Soft blue cushions add comfort to the seating area, while a vase with yellow tulips brings a pop of color. The tranquil view of Deans Pond complements the inviting outdoor space.
Condo in New Seabury
4.94 out of 5 average rating, 72 reviews

Beach Cottage 3nts/4th Free in August,Mashpee MA

GeorgeRating, 5 stars9 months ago
Our second visit. We love the place. Quiet but close to great beaches and the Popponesset Marketplace is 2 minutes walk away, with fish restaurants and small stores with necessities (including wine and beer!). A highlight of this visit was sitting on the patio in the morning and 3 times seeing an osprey dive to the pond and catch a fish.
Guest favorite
An inviting studio space features a large bed positioned beside a modern kitchen. A dining setup is visible, ready for two people. The outdoors showcases a spacious pool area with loungers, while the greenery and sign add a touch of character to the space.
Condo in West Dennis
4.96 out of 5 average rating, 47 reviews

6 Min to Beach - Pool - Private Balcony - Central

NicoleRating, 5 stars6 days ago
My boyfriend and I stayed in this beautiful and quaint condo for a wedding weekend in Dennis and it couldn’t have been a more perfect place with a more perfect location!We both felt safe and comfortable immediately upon arrival and loved spending time outside on the porch and enjoying walking around the area! We would both recommend this stay to anyone!
Guest favorite
A historic stone building is prominently displayed, showcasing a vibrant red entrance and outdoor seating area. Surrounding areas feature neat gardens and pavement that complement the structure. A clear sky and early light enhance the building's architectural details and inviting atmosphere.
Condo in New Bedford
4.98 out of 5 average rating, 58 reviews

Millie's-Historic New Bedford, 2BR, water views

LaurieRating, 5 stars3 weeks ago
We had a great six nights here. The space is super cool, well appointed with comfty beds and super soft towels, and was squeeky clean! We enjoyed the roof deck, the views to the waterfront, and the fireplace--and had an exceptional meal at Cork, too! Our stay was a combination of a work trip plus time to explore New Bedford and the SouthCoast and the location was great for both. Having a dedicated parking space was great, too. We would happily return.

Quick stats about vacation rentals with outdoor seating in Chilmark

  • Total rentals

    100 properties

  • Nightly prices starting at

    R2,154 ZAR before taxes and fees

  • Total number of reviews

    2.5K reviews

  • Family-friendly rentals

    80 properties are a good fit for families

  • Pet-friendly rentals

    40 properties allow pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. Massachusetts
  4. Dukes County
  5. Chilmark
  6. Rentals with outdoor seating